Anti-selective catalytic asymmetric nitroaldol reaction via a heterobimetallic heterogeneous catalyst

Journal of the American Chemical Society

Volumn 131, Issue 38, 2009, Pages 13860-13869

  Nitabaru, Tatsuya ^a   Nojiri, Akihiro ^a   Kobayashi, Makoto ^b   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KISSEI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; CATALYST PREPARATION; CATALYTIC PERFORMANCE; ENANTIOSELECTIVE; HETERO BIMETALLIC COMPLEXES; HETEROBIMETALLICS; HETEROGENEOUS CATALYST; HETEROGENEOUS CONDITIONS; HETEROGENEOUS MIXTURES; HIGH RESOLUTION; NITROALDOL; NITROALKANES; X RAY FLUORESCENCE ANALYSIS;

ALDEHYDES; AMIDES; CATALYSIS; CENTRIFUGATION; CHELATION; INDUCTIVELY COUPLED PLASMA; LIGANDS; NEODYMIUM; PARAFFINS; SODIUM;

CATALYSTS;

ALDEHYDE; ALKANOL; AMIDE; AZIDE; DIMETHYL SULFOXIDE; LIGAND; NEODYMIUM; NITROALKANE; SODIUM;

ALDOL REACTION; ARTICLE; ATOMIC EMISSION SPECTROMETRY; CATALYSIS; CATALYST; CENTRIFUGATION; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; EVALUATION; NITROALDOL REACTION; SEPARATION TECHNIQUE; SUSPENSION; SYNTHESIS; TIME OF FLIGHT MASS SPECTROMETRY; X RAY FLUORESCENCE;

ALDEHYDES; ALKANES; CATALYSIS; ORGANOSILICON COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 70349747004     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905885z     Document Type: Article

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115. At higher temperatures (higher than -20°C), retro-nitroaldol reaction proceeded depending on the substrate used and may decrease the stereoselectivity.
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118. 1H NMR spectrum of the crude mixture, the signals derived from 4aa or 4ea were not observed. Nitroethane (3a) incorporated in the heterogeneous catalyst may be reluctant to be replaced with bulkier nitroalkanes. If initially incorporated nitroethane (3a) reacted with an aldehyde, the amount of the nitroaldol product derived from 3a would be negligible with low catalyst loading.
119. In the reaction using 3c in THF, the heterogeneous catalyst dissolved and the reaction mixture became a clear solution, affording the product with slightly lower stereoselectivity.
120. 13/1m/NaHMDS = 1/2/1.75 ratio gave the best performance.
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124. 2O was used as catalyst, -30°C, THF, 10 equiv of 3a). The yield and stereoselectivity at the specified period of the reaction time were as follows: 3 h, 55% yield, anti/syn = >40/1, 97% ee (anti); 6 h, 72% yield, anti/syn ) >40/1, 98% ee (anti); 12 h, 86% yield, anti/syn = 34/1, 97% ee (anti); 18 h, 89% yield, anti/syn = 31/1, 96% ee (anti); 24 h, 92% yield, anti/syn = 29/1, 96% ee (anti). At temperatures higher than -30°C and with higher catalyst loading (2 mol %), the retro-nitroaldol reaction competitively occurred to decrease the stereoselectivity slightly.